


24 Hours and a Bottle of Jack

by fanfic814



Category: Supernatural
Genre: Anal Fingering, Awkward Sexual Situations, Fluff, Friendship/Love, M/M, Prostate Massage, Rimming, Schmoop, Sexual Experimentation, Sexy Times
Language: English
Status: Completed
Published: 2016-06-29
Updated: 2016-06-29
Packaged: 2018-07-18 22:58:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,684
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7334080
Author URL: https://archiveofourown.org/users/fanfic814/pseuds/fanfic814
Summary: <blockquote class="userstuff">
              <p>A sexually-frustrated Dean and a sex-curious angel decide to experiment.</p>
            </blockquote>





	24 Hours and a Bottle of Jack

**Author's Note:**

> I started this one ages ago and never finished. Thought it was time to fix that.

_**Friday.** _

Dean's bedroom was dark, save for a lavender-scented candle burning on his nightstand.  He didn't even know where the damn thing had come from, alas, his partner for this evening had insisted on it. Though he had willingly agreed to this little arrangement, Dean was beginning to question his judgement as well as his sanity.

As he lay there with his eyes tightly shut, fucking _trembling_  with nervous energy,  Castiel, Angel of the Lord,  was slowly removing his pants.

It wasn't a gradual progression that had led them here - hell, it wasn't even a lust-driven, spur-of-the-moment idea. This evening had been meticulously discussed and planned, boundaries had been drawn, and preparations made.

_What the hell was he thinking?_

::::::::::::

_**Thursday.** _

Dean stumbled into the bunker, entirely too early considering he'd been at the bar since dinner. He was nowhere near drunk, but with a little luck, he would be soon.  He had the place to himself tonight - Sam was out with a girl who had practically thrown herself at him, and that reminder had Dean a little bummed that he'd been striking out left and right lately. So he gathered his keys and what was left of his pride, and headed home to drown his sorrows in cheap whiskey and Internet porn.

He had already had a few drinks, and had just navigated to the Busty Asian Beauties website when a gust of wind sent the papers on his desk flying.

"Hello, Dean. "

"Hey Cas, " Dean replied without missing a beat. He closed his laptop, feeling pretty damn thankful that Cas hadn't shown up fifteen minutes later. He slammed down his shot of whiskey before he spoke again. "What's up?"

"I thought I'd come by to help translate that book Sam was talking about yesterday," Cas said, running his fingers through his hair as if air travel had mussed it.

"Oh. Well Sammy's not here."

Cas nodded slowly. "Mind if I wait?"

Dean snorted in laughter. "You can, but he probably won't be home until morning. I'm sure he's getting lucky by now," he grimaced, pouring himself another shot. He grabbed a second shot glass off his desk and poured one for Cas.

"Have a seat," he motioned.

Cas sat awkwardly on the edge of the bed with his glass in hand.

"Is something wrong, Dean? You seem a bit upset tonight."

"Nah, just feelin' sorry for myself. No big deal. "

Cas threw back his shot and got up to refill their glasses. "What's bothering you? "

Laughing, Dean gratefully accepted his drink. "Just frustrated, " he muttered. "Uh, sexually.  It's been a while. But let's not get into that," he said, rolling his eyes at his own whining.

"How long has it been? "

Usually Dean wouldn't have been so eager to talk, but he was starting to feel that buzz he'd been chasing, and he was always a bit less inhibited once he had a few drinks in him.

"Few months," he said, slamming back his drink and motioning for another. "Just keep striking out with the ladies lately. I don't get it. I'm charming, right? "

Cas nodded. "Yes, Dean."

"I think I'm adorable. "

Cas bit back a smile at Dean's tipsy admission. "Of course you are."

"That girl Sammy's with - I was flirting with her _hard_ , and it was like I didn't even exist! I mean, I'm happy for Sam, but come _on_!" he sighed.

Cas nodded sympathetically. "Perhaps you need to try flirting with a male."

Dean snorted with laughter. "That's not the kind of action I'm looking for, Cas."

"Why not?"

"I... just... I'm just not. " Dean fumbled, reaching for the bottle again.

Cas kicked his shoes off and pulled his legs up onto the bed, leaning his back against the wall as Dean passed him the bottle.

"So you've never been with a man?" he asked curiously.

Dean paused, the glass just inches from his lips. "Define 'been with'," he said before taking a long swig from his glass.

Cas laughed softly. "So you have..."

"I've given and received a few drunken hand jobs on occasion..." he admitted sheepishly.

"Hmm," Cas hummed to himself. "Would you consider being intimate with a male again? Not 'sex' per se, but..."

Dean shrugged. "I don't know. I guess it depends on what you mean by 'intimate'.  And it depends on the guy."

Cas stared at him earnestly. "What if..." he started. He shook his head and tried again. "What about me?"

Dean nearly choked on his whiskey. "What?"

"Well, _you're_ feeling frustrated, _I've_ never been with a male. I'm curious about human sexuality, Dean.  I've done a lot of reading, and I'm interested in experimenting."

Dean paled a bit, but he didn't say 'no'. "Didn't get enough of human sexuality with April?" he scoffed.

Cas sighed. "Being with April was nice, but I would like to also explore the male form. I can't seem to bring myself the same kind of pleasure I had with her, and I'd like to... I don't know... Explore.  See what works for others, and maybe try it on myself."

"Oh."  Dean swallowed hard.  He was just drunk enough to be able to talk about this, and yet sober enough to not blindly agree. "What do you have in mind?"

Cas shrugged.  "Kissing and touching mostly, with hands, mouth... I don't know exactly.  But it might settle my curiosity and help your frustration at the same time."

Dean nodded uncertainly, though his dick was clearly into it.  Sure, he'd fooled around with a guy a time or two, but this was _Cas_. Could they even _do_ something like that without it getting awkward?   Would he even be able to look him in the eye afterward?

"Don't feel obligated, of course," Cas continued casually.  "I was just offering a possible solution to both of our problems."

Dean nodded again.  Hell, like he could turn down an offer of free, no-strings-attached action?  He knew better than to look a gift horse in the mouth.  Besides, this was like...  _doing Cas a favor_.  It wasn't a big deal.  And if he got a little out of it, it was just a bonus. They were friends! They could handle this...

"Okay," Dean said tentatively. "But no ass stuff." After all, he wasn't really into that sort of thing. Obviously.

"Okay, " Cas agreed.

"So um. How do you want to do this? "

Cas smiled. "Not tonight. You're way too intoxicated. Tomorrow. I'll come by around ten. You'll be awake, right?"

Dean nodded.

"Good. You should sleep that off, Dean. I'll see you tomorrow. "

::::::::::::::

_**Friday.** _

So here they were, Cas slowly but surely sliding Dean's pants down his legs. He yanked them off over his feet, and his fingers gripped the waistband of his boxers, making Dean tense up. He may have been too drunk last night, but he was way too damn sober today. Cas had insisted he not drink so that his judgement wasn't clouded, and for whatever reason, he'd listened.

He took a long, deep breath as the shorts slipped away, his cock springing free of the fabric that had been restraining it, and Cas took a shuddering breath of his own.

"Dean," he breathed. "You're even more beautiful than I imagined..."

Cas was staring like he was about to devour him in a slow, savoring way, and Dean couldn't stop the flush of pink rushing over his body.

"Cas, this is going to sound weird, but can you please get naked too? I'm feeling kind of vulnerable here," Dean admitted weakly.

"Oh," Cas said. "If that makes you more comfortable..." He closed his eyes as if he were focusing hard, and his clothing disappeared, reappearing folded neatly on top of Dean's dresser.

"Ohh," Dean gasped. Shit, maybe he'd just made things worse. But he didn't have time to think about that as two strong, firm hands suddenly began caressing up and down his chest.

While Dean was still trembling a bit at the intimacy, Cas didn't hesitate at all, his strong hands wandered his body confidently as if he owned it, curiously watching Dean's every expression.

"You're absolutely lovely, Dean, " Cas murmured, splaying his fingers and dragging them down his torso.  "You have freckles on your shoulders too, " he whispered, smiling in awe of this new discovery. "And across your clavicle ..." he gently thumbed over his collarbone, making Dean shiver.

Dean's entire body was already singing with a mixture of anxiety and anticipation.   Dammit, he should not be so turned on already. And why the hell was he still trembling?

Cas nudged his knees apart and knelt between them, lying his body on top of Dean's. He groaned softly as their cocks pressed against each other, and he studied Dean's face intently.  "You look absolutely gorgeous with your face all flushed pink like this," Cas murmured.

"Cas," Dean protested.  Okay, he could deal with the touching, but the sweet talk had to go.  He felt like he was under a magnifying glass with Cas examining him so carefully.  Sure he might seem pulled together from a distance, but up close up he was a hot mess.   He sure as hell wasn't worthy of this body worship.

"But it's true."

Dean bit his lip and closed his eyes, trying to pretend this was any other hookup he'd ever had, and desperately trying to convince himself that he didn't like it so much.  He had to remember that this was just an experiment for Cas - just curious exploration, nothing more.  Cas's hand grazed the side of his face, and his eyes fluttered closed just before Cas leaned in to press soft, gentle little kisses against his lips.  His body was already begging for more, and Cas was happy to indulge him.  

Something about this whole scenario made him feel like his middle school self, fumbling through his first kiss. He was excited and terrified and confused all at once.  This was supposed to be fun, no-strings attached handjobs and shit!  Why did it already feel like something more?  

Maybe it was the way Cas kept looking at him with those wide, imploring blue eyes, like he was something delicate and precious.  Who the hell did he think he _was_ , looking at him like that?  He had been with a lot of women, but the only one who ever looked at him like that was Lisa, and even that had made him feel uncomfortable.

When Cas's tongue gently began prodding at his lips, he opened them, allowing Cas to dominate his mouth with tiny, teasing little kitten licks. Just as he started relaxing into it, Cas moved away, trailing sucking little kisses across his jaw and down his neck.

Dean had always been a sucker for neck kisses, and he tried hard to stifle a moan as Cas hit that sweet spot that made him shivery.

"Right there?" Cas asked innocently, licking over the area again before giving it a little suck and nibble.

"Ahhh, shit," Dean whimpered.

Cas made a mental note. "I'll take that as a 'yes'." He continued lavishing him with kisses, gently moving down his chest.

"Cas, what are you doing? " Dean finally managed.

"What do you mean? " Cas asked, glancing up from his position near Dean's stomach.

Dean struggled awkwardly for the right words. "I thought you wanted to uh... fool around."

"Of course I do.  But isn't this what most people do leading up to it?  Foreplay, I think you call it."

Dean shrugged. "Well yeah, I guess so, but..."

"You don't like it? " Cas asked.  He cocked his head and gave him that slightly hurt and confused look that always seemed to rip Dean's heart out.

Dean swallowed hard. "Of course I like it..."  Goddammit, he liked it way too much, and it scared the shit out of him.

"Good." Cas began licking a line down his abs as his hands kept stroking everywhere he could reach.  "So beautiful, Dean," he whispered.  His fingers worked over an old scar gracing Dean's ribs and Dean felt a brief warming sensation as the skin healed.  When Dean whimpered as he kissed at his hipbones, Cas sucked a little red welt there, causing him to groan.

"Fuck," Dean whispered.   His dick was weeping and standing at attention just inches from Cas's face, but Cas paid it no mind.  He was running his fingertips down along the inside of his thighs now, and Dean's legs jerked in response.

"Cas, you're killin' me," he groaned again.

Cas smiled warmly and lowered his body on top of his again, this time deepening his kisses.

Sure, Dean liked a filthy kiss or two when he was in the throes of passion, but this tender, gentle caressing and kissing was making him absolutely crazy. It felt... weird.  Not _bad_ -weird, just... weird. This was the type of kissing people in a new relationship did. And goddammit, Cas hadn't really even touched him yet. Fuck, he was getting frustrated. If Cas wasn't going to make a move soon, he just might do it himself.

"Your lips are so soft..." Cas whispered as he gently nibbled at Dean's bottom lip. "You have beautiful lips."

"Cas," Dean rasped, "you gotta stop calling me beautiful.  And you need do something, or get up so I can do it myself."

Cas chuckled fondly. "Yes, Dean. " He propped himself up and worked a trail of kisses back down his chest, pausing to let his pointy tongue flick over a stiff nipple.  "But you _are_ beautiful..."

Dean grunted and fisted a hand in the back of his hair, gently guiding him down between his legs, as Cas grinned.

"So impatient," he murmured, as Dean's hips rocked forward.  "So you like that?" he asked innocently, reaching up to tease the nipple between his fingers.

"Cas," Dean growled.

"Alright, " Cas whispered. His hand softly wrapped around his cock and Dean let out a ridiculously loud moan.

"So soft," Cas mused, thumbing over the velvety soft head. He tentatively licked at the moisture glistening at the tip, and glanced up just in time to see Dean's face contort in pleasure.

"I like watching you like this," Cas breathed. "You're so raw and vulnerable. It's nice to see this side of you."

Dean blushed again. He wished Cas would stop talking like that. It was entirely too intimate for a guy who was just there to observe a male body.

Cas's tongue flicked over the head again, then he sucked, drawing another shivering moan out of Dean's mouth. He let his hands wander as he licked at him, massaging his hips and inner thighs before working a hand between his legs and fondling his balls.

Dean groaned again. For someone who had never done this before, Cas sure knew how to push all of his buttons. He lay there with his eyes tightly closed, trying not to think too much about how awkward this was going to be come tomorrow. Cas was gently kneading his balls and his mouth was so hot and tight around his cock, he knew he wasn't going to last long.

"C...Cas..." he gasped.

Cas suddenly pulled back. "Shhh. Not yet."

Dean whined in frustration. "What are you..."

Cas shushed him again and bent Dean's legs at the knee, and before Dean could even register what was happening, Cas's tongue was flicking below his balls and tracing around the pink puckered flesh below.

"Whaaat the fuck?" Dean choked. He was not expecting _that_. Jesus, he liked to think he was a little kinky, but he could honestly say he'd never had _that_ licked. It felt surprisingly good, and Cas seemed to notice as he hummed happily.

"Do you like that? " he asked in a husky voice.

Though he didn't really want to admit it, his head nodded frantically.

"Good," Cas breathed. His tongue circled a few more times and then pressed into him and Dean yelped in surprise.

"C...Cas. No ass stuff, remember? " Dean said, trying to talk himself out of the fact that he was liking this way more than he would ever confess.

Cas pulled back and nuzzled at his cock, then licked at the salty, musky liquid forming at the tip. "But you obviously like it, Dean, " he whispered. "Please. Let me do this for you."

Dean's hips stuttered again. He was so damn out-of-his-mind horny he was practically humping the air. "I... uh..."

Cas sucked him into his mouth and his hands wandered up Dean's chest, tweaking gently at his nipples. "You need the release," he whispered. "All that pent-up sexual tension... I can make you climax harder than you ever have. Let me show you, Dean. "

"Yeah. Yes! Okay! " Dean panted. Anything to just _get off_ already. This was slow, delicious torture and he was not a patient man.

"Good," Cas purred. "Do you have lubrication? " he murmured.

Dean pointed to the nightstand drawer, and seconds later, he quivered as he felt a slick finger tracing around his entrance. "Ahh, shit.  On second thought, I don't know if I can do this," he suddenly blurted.

Cas started kissing he way back up his chest.  "You can," he whispered, letting their lips meet again in a long, sensual caress.  "Let me take care of you, Dean. I promise it's going to feel good," he murmured, peppering his jaw with kisses.

Dean nodded nervously.  Jesus, what was happening to him?  This whole thing was making him feel a bit too mushy.  This was supposed to be a quickie no-strings fling, but he was feeling all sorts of things that he shouldn't be.  
  
Cas didn't move from his position, still kissing as he let his finger slide back down between his cheeks.  "Just relax," he whispered.    
  
Dean closed his eyes as Cas rubbed little circles around him, gently letting the pad of his finger dip in and out, just enough to give him a taste.  He groaned as more of Cas's finger breached the tight ring of muscle and his entire body clenched in response.   
  
"Shhh.  It'll get better."    
  
Dean took a deep breath and slowly let his body go slack as Cas paused so that he could get used to the new sensation.    
  
"Good," he whispered encouragingly, his breath hot against Dean's lips.  "Look at me."  
  
Dean's eyes opened to see Cas's dark blue ones staring intently at him, as if they were boring right through to his soul.   For all Dean knew, they _were_.  But dammit, he really needed to stop looking at him like that. "Cas..." he started, but it came out more like a whimper.  
  
"That's good, Dean," Cas hushed.  He slowly began moving his finger in and out, and Dean was surprised that it wasn't as bad as he had anticipated.  He continued until he could feel Dean's body start to respond to his touch.  "Now how does this feel?"  He crooked his finger and began gentle little caresses inside of him, at a little spot Dean could only assume was his prostate.   
  
"I don't know," Dean struggled.  "Weird?  I feel like I'm gonna piss."    
  
Cas just laughed and continued slow, gentle rubbing motions for a few minutes until Dean's entire body suddenly buckled.   
  
"Oh!  Fuck!" he gasped.    
  
Cas grinned and kissed him hard, encouraging his mouth to part again and tangling their tongues together until he was nearly devouring him.    
  
"Fuck, Cas," Dean panted as Cas came up for air.    "I'm...  Uhh..."  Hell, he didn't know what was happening.  He was hot.  So fucking hot, and his blood pressure felt like it had gone through the roof. His dick was leaking like crazy, and he felt on the edge of orgasm, but he couldn't come just yet.    
  
"Shhh.  You're doing so well.  Just let it happen," Cas whispered.    
  
Tiny little tremors shot through Dean's body and his hands suddenly gripped at the sheets.  "What the fuuuck?" he wailed. He was pretty sure he had just jizzed a little but he was still freakin' _hard_.   
  
Cas smirked and gave him a final kiss on the cheek before returning to the position between his legs.  His finger kept stroking that magical spot while he lowered his mouth down around his cock and sucked, and Dean absolutely keened with pleasure.   
  
"Cas... fuck!  Fuck! Oh god..."    
  
Cas hummed deep in his throat as Dean began to come, swallowing around him and making him moan louder.   
  
As Dean finally stilled, Cas kissed his way back up his body and lay down next to him, watching Dean struggle to catch his breath.

"That was lovely, Dean.  You're absolutely breathtaking like this," he murmured as he delicately ran his fingers through Dean's sweat-slicked hair.   
  
"Caaas," Dean protested tiredly.  He was utterly fucked out, but that didn't stop him from groaning as Cas continued to call him all these things he wasn't.  He struggled, still a bit breathlessly, to sit up.  "Alright.  Your turn.  You wanted to know what does it for you," he said, pushing Cas flat onto his back.   "Oh!" he gasped as he noted that Cas had obviously already come.   
  
Cas blushed.  "Think I already figured that out..."  With a wave of his hand, the mess was gone.  He pulled Dean back down onto the bed and snuggled in close to his back, tightening an arm around his waist.   
  
Dean was too damn exhausted to complain about being the 'little spoon' today.  And though he would never say it out loud, he was really feeling the need to be held after all of that. So he closed his eyes and relaxed into Cas's arms.   
  
"So what did it for you?" he murmured sleepily.   
  
"You."  
  
"What part?"  
  
"All of it. Watching you, touching you, being with you.  I love you, Dean."  
  
Dean's eyes flew open again and his body clenched.  "Cas, you can't just say shit like that!" he muttered, feeling his heart suddenly hammering in his chest.  
  
"But it's true," Cas said simply, his lips kissing and nipping softly against Dean's shoulder.    
  
Dean huffed a little in surprise.  "Oh.  I uh..."  he cleared his throat nervously.  "Um... Cas, I..."  
  
"I know," Cas whispered softly.  "Rest now, Dean."


End file.
